Iniparib

Base Information

• Chemical Name: Iniparib
• CAS No.: 160003-66-7
• Deprecated CAS: 937799-96-7
• Molecular Formula: C7H5IN2O3
• Molecular Weight: 292.033
• Hs Code.: 2924299090
• European Community (EC) Number: 685-396-9
• UNII: 2ZWI7KHK8F
• DSSTox Substance ID: DTXSID30166784
• Nikkaji Number: J680.388A
• Wikipedia: Iniparib
• Wikidata: Q260286
• NCI Thesaurus Code: C62526
• Metabolomics Workbench ID: 154652
• ChEMBL ID: CHEMBL1170047
• Mol file: 160003-66-7.mol

Synonyms:4-iodo-3-nitrobenzamide;BSI 201;BSI-201;BSI201;iniparib

Chemical Property of Iniparib

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.696
• Boiling Point: 344.754 °C at 760 mmHg
• PKA: 14?+-.0.50(Predicted)
• Flash Point: 162.302 °C
• PSA: 88.91000
• Density: 2.056 g/cm³
• LogP: 2.52180
• Storage Temp.: room temp
• Solubility.: DMSO: soluble5mg/mL, clear
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 291.93449
• Heavy Atom Count: 13
• Complexity: 228

Purity/Quality:

98% min ^*data from raw suppliers

Iniparib ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36-43
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C=C1C(=O)N)[N+](=O)[O-])I
• Recent ClinicalTrials: Treatment Extension Study for Patients Who Have Previously Participated and Have Benefited From Iniparib in a Clinical Trial
• Recent EU Clinical Trials: International, Multi-Center, Open-label, Treatment Extension Study of Iniparib as Monotherapy or in Combination Chemotherapeutic Regimens in Cancer Patients Who Have Derived Clinical Benefit From Iniparib Following Completion of a Phase 1, 2 or 3 Parental Study
• Description: Iniparib (160003-66-7) was originally thought to be a PARP1 inhibitor but this is controversial.1,2?Inhibits ionizing radiation-induced single-stranded DNA break repair in lymphoid cell lines?in vivo.3?Inhibits growth of certain breast cancer cell lines?in vitro. Iniparib non-selectively modifies cysteine-containing proteins in tumor cells.4
• Uses: Iniparib is an irreversible PARP1 inhibitor. Studies show that potential therapeutic agent for the treatment of cancer, including triple-negative breast cancer. Iniparib (BSI-201) is an antineoplastic originally thought to be a poly(ADP-ribose) polymerase-1 (PARP-1) inhibitor. Recent studies indicate Iniparib is not a PARP-1 inhibitor, and its mechanism of action is currently unknown. Poly(ADP-ribose) polymerase (PARP) is a critical DNA repair enzyme involved in DNA single-strand break repair via the base excision repair pathway. PARP1 is activated by DNA damage. Inhibiting its activity has been linked to synthetic lethality and loss of either of the breast cancer susceptibility genes, BRCA1 and BRCA2. BSI-201 is an irreversible, noncompetitive inhibitor of PARP1 that disrupts binding between PARP1 and DNA by interacting with the DNA binding domain. It produces rapid apoptosis in various cancer cell lines with IC50 values ranging from 40-128 μM and is not toxic in Syrian hamsters at doses as high as 200 mg/kg. In phase II clinical studies, BSI-201, in combination with carboplatin and gemcitabine, has produced promising results in "triple-negative" breast cancers, increasing median overall survival from 7.7 months to 12.3 months.

Technology Process of Iniparib

There total 6 articles about Iniparib which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 62.0%

4-iodo-3-nitrobenzoyl chloride (532406-56-7) → 4-iodo-3-nitrobenzamide (160003-66-7)

Guidance literature:

With ammonium hydroxide; In tetrahydrofuran; for 1h; Schlenk technique; Inert atmosphere;

DOI:10.1039/c8ob01095a

Reference yield: 54.0%

4-bromo-3-nitrobenzamide (879-93-6) → 4-iodo-3-nitrobenzamide (160003-66-7)

Guidance literature:

With tributylphosphine; sodium iodide; nickel dibromide; In 1-methyl-pyrrolidin-2-one; at 140 ℃; for 18h; Inert atmosphere; Molecular sieve; Sealed tube;

DOI:10.1039/c2cc30956d

Reference yield: 40.5%

ammonium hydroxide (1336-21-6) + 4-iodo-3-nitrobenzoic acid (35674-27-2) → 4-iodo-3-nitrobenzamide (160003-66-7)

Guidance literature:

With thionyl chloride; In water; N,N-dimethyl-formamide; acetonitrile;

upstream raw materials:

4-iodo-3-nitrobenzoic acid

ammonium hydroxide

4-bromo-3-nitrobenzamide

4-iodo-3-nitrotoluene

Refernces

• 1、 Fu, Zhengjiang,Jiang, Ligao,Zuo, Qianming,Li, Zhaojie,Liu, Yanzhu,Wei, Zhenhong,Cai, Hu. "Inexpensive NaX (X = I, Br, Cl) as a halogen donor in the practical Ag/Cu-mediated decarboxylative halogenation of aryl carboxylic acids under aerobic conditions". . p. 5416 - 5421. Retrieved 2018/08/12.
• 2、 -. "Synergistic compositions useful as anti-tumor agents". . . Retrieved 2008/06/13.